After reading Live from New York and seeing a biography on Tim Allen, Landau wanted to move from improv to stand-up comedy. He had only considered pursuing it before until his classmate and later wife, and comedian Martin Butler, convinced him to go on stage, which took place at Mark Ridley's Comedy Castle in April 2004.[3][1] Butler landed Landau a spot at the Ann Arbor Comedy Showcase.[3] Landau once ran a comedy improv and stand-up show at the Village Idiot with his wife and a group of other comedians.[2]

In 2004, Landau won a comedy competition in Lansing which secured him work in other clubs.[3] In 2005, he opened for Chappelle at an arena show which he later cites as a career highlight.[1]

In 2014, Landau participated on the eighth season of the comedy television series Last Comic Standing, ending up as a finalist. He later revealed that "I got kind of screwed over on a very national level because Roseanne didn't get a joke."[2] Landau has appeared on Gotham Comedy Live on AXS three times.[2]